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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN b = (7) Å c = (13) Å = (10) V = (3) Å 3 Z =4 Mo K radiation = 2.78 mm 1 T = 297 (2) K mm Substitutional disorder in a hypervalent diorganotin(iv) dihalide Adina Rotar, Richard A. Varga* and Cristian Silvestru Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Str. no. 11, RO , Cluj Napoca, Romania Correspondence richy@chem.ubbcluj.ro Received 22 November 2007; accepted 26 November 2007 Data collection Bruker SMART APEX CCD areadetector diffractometer Absorption correction: multi-scan (SAINT-Plus; Bruker, 2000) T min = 0.452, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 6916 measured reflections 1746 independent reflections 1693 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.36 e Å 3 min = 0.47 e Å 3 Key indicators: single-crystal X-ray study; T = 297 K; mean (C C) = Å; disorder in main residue; R factor = 0.026; wr factor = 0.060; data-to-parameter ratio = Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA The structure of bromidochloridobis[2-(dimethylaminomethyl)phenyl]tin(iv), [SnBr 0.65 Cl 1.35 (C 9 H 12 N) 2 ], contains two 2- (Me 2 NCH 2 )C 6 H 4 units bonded to a Sn atom which lies on a twofold axis. The compound exhibits substitutional disorder of the halide atoms bonded to the Sn, with 1.35 occupancy for Cl and 0.65 for Br; it is isomorphous with the corresponding dichloride. The Sn atom is hexacoordinated with a (C,N) 2 SnX 2 (X = Cl/Br) distorted octahedral core as a result of the strong intramolecular N!Sn coordination trans to the Sn X bonds (N1 Sn1 X1 = ). As a result of the intermolecular contacts, viz. HX and Hbenzene interactions, the molecules are arranged in a three-dimensional supramolecular manner in the crystal structure. Related literature For related literature see Varga et al. (2001, 2005, 2006, 2007); Rotar et al. (2007); Emsley (1994); IUPAC (1979). C3 H3Cg1 ii (1) 123 C4 H4Cl1 ii /Br1 ii (5) 173 C6 H6Cl1 iii /Br1 iii (3) 132 Symmetry code: (ii) 1 2 þ x, 1 2 þ y, z, (iii) 2 x, 1 y, 1 z. Cg1 is the centroid of the benzene ring C1 C6. Data collection: SMART (Bruker, 2000); cell refinement: SAINT- Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publcif (Westrip, 2007). Financial support from the National University Research Council (CEEX 63/2006) is greatly appreciated. We also thank the National Center for X-Ray Diffraction, Cluj-Napoca, for help with the solid-state structure determination. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GD2029). Experimental Crystal data [SnBr 0.65 Cl 1.35 (C 9 H 12 N) 2 ] M r = Monoclinic, C2=c a = (15) Å References Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Bruker (2000). SMART (Version 5.625) and SAINT-Plus (Version 6.29). Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2001). SHELXTL. Version Bruker AXS Inc., Madison, Wisconsin, USA. Emsley, J. (1994). Die Elemente. Berlin: Walter de Gruyter. IUPAC (1979). Nomenclature of Organic Chemistry. Oxford: Pergamon Press. Rotar, A., Varga, R. A. & Silvestru, C. (2007). Acta Cryst. C63, m355 m356. Varga, R. A., Rotar, A., Schuermann, M., Jurkschat, K. & Silvestru, C. (2006). Eur. J. Inorg. Chem. 7, Varga, R. A., Schuermann, M. & Silvestru, C. (2001). J. Organomet. Chem. 623, Varga, R. A. & Silvestru, C. (2007). Acta Cryst. C63, m48 m50. Varga, R. A., Silvestru, C. & Deleanu, C. (2005). Appl. Organomet. Chem. 19, Westrip, S. P. (2007). publcif. In preparation. doi: /s Rotar et al. m45
2 supporting information [ Substitutional disorder in a hypervalent diorganotin(iv) dihalide Adina Rotar, Richard A. Varga and Cristian Silvestru S1. Comment During our work on hypervalent organotin(iv) compounds with the [2-(Me 2 NCH 2 )C 6 H 4 ]Sn fragment (Varga et al., 2001, 2005, 2006, 2007, Rotar et al. 2007), the title compound (I) was isolated. It contains two 2-(Me 2 NCH 2 )C 6 H 4 units bonded to a tin atom which lies on a twofold axis of the space group C2/c. The compound exhibits substitutional disorder of both halide atoms bonded to the Sn with chlorine being the major (1.35) and the bromine the minor (0.65) component. The structure of [2-(Me 2 NCH 2 )C 6 H 4 ] 2 SnCl 2 was also determined (Varga et al., 2001) and is isomorphous with the title compound. Both have space group C2/c; the cell constants as well as the volume differ slightly (0.39% increase for the title compound) as the result of the presence of a different halide in the molecular unit. The molecules of the compound feature a metal atom strongly coordinated by two nitrogen atoms of the pendant arms [Sn N1 = 2.64 (1) Å; the Sn N distance exceeds the sum of the covalent radii for the corresponding atoms, Σ cov (Sn,N) = 2.1 Å (Emsley, 1994)] trans to an Sn halogen bond (N1 Sn1 X1 = ). This results in a (C,N) 2 SnX 2 (X = Cl/Br) core in the title compound with a trans-snc 2 fragment, while the N and X atoms are cis positions (Fig. 1). The octahedral geometry around the Sn atom is distorted from the ideal geometry as a consequence of the small 'bite of the pendant arm ligand [C1 Sn1 N1 = 71.4 ] and the steric repulsion between the organic groups bonded to the Sn atoms. All these features are similar to the corresponding dichloride. As a result of the intramolecular coordination of the nitrogen to the tin atom a five-membered SnC 3 N ring is formed. This ring is not planar but is folded along the Sn(1) C methylene axis with the N atom out of the best plane defined by the residual SnC 3, thus inducing planar chirality, with the phenyl ring as chiral plane and the nitrogen as pilot atom (IUPAC, i i 1979). Indeed, the compound crystallizes as a racemate, i.e. a mixture of R N1 R N1 and S N1 S N1 [symmetry code: (i) 2 - x, y, z]. In the crystal of the title compound intermolecular interactions, i.e. hydrogen bond type interactions and H phenyl interactions (Fig. 2), give rise to a supramolecular array. If only chlorine is considered than layers are built of the same type of isomer [H4 X1 ii = 2.87 Å, H3 Cg1 ii = 3.19 Å; symmetry code: (ii) -1/2 + x, 1/2 + y, z] along the ab plane (Fig. i i 3). If bromine is taken into account, than alternating parallel layers of R N1 R N1 and S N1 S N1 isomers are bridged through weak H6 X1 iii [3.02 Å; symmetry code: (iii) 2 - x, 1 - y, 1 - z] interactions resulting in a three-dimensional supramolecular architecture (Fig. 4). S2. Experimental The title compound was isolated as a by-product of the reaction between [2-(Me 2 NCH 2 )C 6 H 4 ]SnCl 2 and [2,6-(Me) 2 C 6 H 3 ]MgBr, due to partial halide exchange. sup-1
3 S3. Refinement All hydrogen atoms were placed in calculated positions using a riding model, with C H = Å and with U iso = 1.5U eq (C) for methyl H and U iso = 1.2U eq (C) for aryl H. The methyl groups were allowed to rotate but not to tip. The two halide atoms were refined as substitutional disorder between chlorine and bromine, with 1.35 occupancy for Cl and 0.65 occupancy for Br. Figure 1 A view of title compound showing the atom-numbering scheme at 30% probability thermal ellipsoids for (R N,R Ni )-(I) isomer [symmetry code: (i) 2 - x, y, z]. H atoms are drawn as spheres of arbitrary radii. sup-2
4 Figure 2 Intermolecular interactions [shown as dashed lines, black for H X (X = Cl/Br), red for H phenyl]. Only H involved in interactions are showed. Symmetry codes: (i) 2 - x, y, z, (ii) -1/2 + x, 1/2 + y, z, (iii) 2 - x, 1 - y, 1 - z. Figure 3 View of the two-dimensional layer formed through H X and H phenyl interactions along c axis. Only H involved in interactions are showed. sup-3
5 Figure 4 Crystal packing showing the three-dimensional supramolecular architecture along a axis. Only H involved in interactions are showed. bromidochloridobis[2-(dimethylaminomethyl)phenyl]tin(iv) Crystal data [SnBr 0.65 Cl 1.35 (C 9 H 12 N) 2 ] M r = Monoclinic, C2/c Hall symbol: -C 2yc a = (15) Å b = (7) Å c = (13) Å β = (1) V = (3) Å 3 Z = 4 Data collection Bruker Smart APEX CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator phi and ω scans Absorption correction: multi-scan (SAINT-Plus; Bruker, 2000) T min = 0.452, T max = F(000) = D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 3754 reflections θ = µ = 2.78 mm 1 T = 297 K Block, colourless mm 6916 measured reflections 1746 independent reflections 1693 reflections with I > 2σ(I) R int = θ max = 25.0, θ min = 2.5 h = k = 9 9 l = sup-4
6 Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 108 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.36 e Å 3 Δρ min = 0.47 e Å 3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Occ. (<1) Br (5) (9) (5) (3) (3) Cl (5) (9) (5) (3) (3) Sn (4) (12) C (18) (4) (2) (7) C (2) (4) (2) (8) H * C (2) (5) (3) (9) C (2) (5) (3) (10) H * C (3) (6) (3) (12) H * C (2) (6) (3) (12) H * N (19) (4) (2) (8) C (2) (6) (3) (11) H7A * H7B * C (3) (5) (3) (13) H8A * H8B * H8C * C (3) (7) (3) (15) H9A * H9B * H9C * sup-5
7 Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Br (5) (5) (6) (4) (4) (4) Cl (5) (5) (6) (4) (4) (4) Sn (18) (18) (19) (13) C (16) (17) (19) (13) (15) (14) C (19) (2) (2) (15) (16) (16) C (19) (2) (2) (17) (17) (18) C (2) (3) (2) (2) (2) (2) C (2) (3) (3) (2) (2) (3) C (2) (3) (3) (2) (2) (2) N (18) (2) (17) (15) (14) (15) C (2) (3) (2) (2) (18) (2) C (3) (3) (3) (2) (3) (2) C (3) (4) (2) (3) (2) (3) Geometric parameters (Å, º) Br1 Sn (7) C4 H Sn1 C (3) C3 H Sn1 C1 i (3) N1 C (5) Sn1 Cl1 i (7) N1 C (5) Sn1 Br1 i (7) N1 C (5) C1 C (5) C7 H7A C1 C (5) C7 H7B C6 C (5) C8 H8A C6 H C8 H8B C2 C (5) C8 H8C C2 C (5) C9 H9A C5 C (6) C9 H9B C5 H C9 H9C C4 C (6) C1 Sn1 C1 i (17) C4 C3 C (4) C1 Sn1 Cl1 i (9) C4 C3 H C1 i Sn1 Cl1 i (9) C2 C3 H C1 Sn1 Br1 i (9) C7 N1 C (3) C1 i Sn1 Br1 i (9) C7 N1 C (3) Cl1 i Sn1 Br1 i 0.00 (4) C8 N1 C (3) C1 Sn1 Br (9) N1 C7 C (3) C1 i Sn1 Br (9) N1 C7 H7A Cl1 i Sn1 Br (4) C2 C7 H7A Br1 i Sn1 Br (4) N1 C7 H7B C2 C1 C (3) C2 C7 H7B C2 C1 Sn (2) H7A C7 H7B C6 C1 Sn (2) N1 C8 H8A C5 C6 C (3) N1 C8 H8B sup-6
8 C5 C6 H H8A C8 H8B C1 C6 H N1 C8 H8C C1 C2 C (4) H8A C8 H8C C1 C2 C (3) H8B C8 H8C C3 C2 C (3) N1 C9 H9A C4 C5 C (4) N1 C9 H9B C4 C5 H H9A C9 H9B C6 C5 H N1 C9 H9C C5 C4 C (4) H9A C9 H9C C5 C4 H H9B C9 H9C C3 C4 H C1 i Sn1 C1 C (3) C6 C1 C2 C (4) Cl1 i Sn1 C1 C (3) Sn1 C1 C2 C7 4.9 (5) Br1 i Sn1 C1 C (3) C1 C6 C5 C4 0.1 (6) Br1 Sn1 C1 C (3) C6 C5 C4 C3 1.5 (7) C1 i Sn1 C1 C (3) C5 C4 C3 C2 0.8 (7) Cl1 i Sn1 C1 C (3) C1 C2 C3 C4 1.3 (7) Br1 i Sn1 C1 C (3) C7 C2 C3 C (4) Br1 Sn1 C1 C (3) C8 N1 C7 C (4) C2 C1 C6 C5 2.0 (5) C9 N1 C7 C (4) Sn1 C1 C6 C (3) C1 C2 C7 N (5) C6 C1 C2 C3 2.6 (6) C3 C2 C7 N (4) Sn1 C1 C2 C (3) Symmetry code: (i) x+2, y, z+1/2. sup-7
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